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Hey friend, Summer is almost over and you know what that means. Time to talk about Fall Trends this season we're doing something different because I don't want to just tell you about the fall trends I want to show you. So instead of our usual 10 Wearable Trends podcast episode, I'm hosting a live Fall Trends Preview party where I'm going to share the trends that women over 40 will be wearing this season. You'll learn about five big style stories you're going to see this fall and the pieces you need to bring them to life. I'll talk about the key colors, accessories and silhouettes for the season and tell you where to spend and save on the trends. Plus, there will be time at the end to ask your fall trend questions and get real time answers. It's happening Thursday, September 4th at 7pm Central Time. Just head to your everyday style.com fall to register for this free event. Even if you can't attend the preview party live, be sure to register. As long as you're on the list, I'll send you the replay and the shopping links. Again, it's going down Thursday, September 4th at 7pm Central and you can register at your everyday style.com fall I'll see you in September foreign it's week nine of the everyday Style School Summer Shorts. That's our weekly summer series sharing a quick style thought or tip to help you save money, save time, and get the wardrobe you've always wanted. Jennifer I'm your host, Jennifer Macchi. Mary I've been dressing Women for over 25 years and I'm on a mission to help you love the way you look every single day. And speaking of that, today's tip is a practical strategy that will help you love the way you look more often. And that is you ready for it? Here it is. Spend your money where you spend your time. Let's hop into the Wayback Machine for a minute for a little story. One of the clients I worked with very early on in my styling business was a woman who wanted help looking more put together in her daily life. We didn't do a closet edit because she said that she had absolutely nothing. She was really struggling just to get dressed every day, so there was no point to go through clothes she didn't have. We just needed to completely start from scratch, which, okay, cool, we can do that. We met up for our shopping trip and we were strategizing before we got started talking about her budget, items she absolutely needed to get, and some things that she hoped to find if time and budget Allowed. She told me that her budget for the shopping trip was $500, which isn't nothing, right? But she was expecting this to be her big wardrobe shop for the year. And in that context, $500 isn't much, especially if you're starting from scratch. There were a bunch of things on her must have list, but two really stood out. These were the top two on that must have list. First, jeans. She was a self described jeans and T shirt woman and she said she lived in jeans, but she only had one pair and she didn't really even like those. Okay, no problem. That's where I started with about 90% of my clients. The other must have piece for our trip was a dress for a black tie event she and her husband went to every year. I don't remember what it was. I think it was a charity or something that was really important to them. Doesn't matter. I asked her if the dress was part of the budget or in addition to, and she told me it was part of it. She had already factored that in to the $500 she felt comfortable spending. Now, I was always very, very respectful of budgets, and I love a challenge, but in my head I was like, whoop, there goes the nice to have list and probably most of the need to have things too. I explained to her that $500 probably wasn't going to go as far as she had hoped, but we would do our best. And then we talked about her budget in a little bit more detail and specifically how she wanted to allocate her dollars. She told me that she was comfortable spending two to three hundred dollars on the dress. This event was really important to her and she wanted to look great for it. Okay, cool. Then she told me she was comfortable spending around $30 on jeans. Definitely no more than 50. She told me this is how she had been doing it in the past and it was working for her. Obviously, the fact that I was there having this conversation meant that it wasn't actually working for her, but that's not the point. The point and the reason I wanted to share this with you was that this was an important lesson for me as a stylist because I was still new and starting to learn the common mistakes that women were making in their wardrobes and how to fix them. And a little light bulb went off in my head and said, well, wait, of course she can't get dressed. She doesn't have money for the things that she wants to wear every day. Now, this client was an extreme example, but since then I have Worked with countless women who were doing the same thing to varying degrees, leading to various levels of struggle. But the problem was the same. There was a disconnect between where their wardrobe dollars were going and and where their time was going. So there are really two parts to this idea that you should spend your money where you spend your time. And today we're going to talk about both of them, as well as how to right, size your wardrobe so you can like the way you look more often and stop wasting money on clothes that aren't worth the investment. The first and often the most obvious issue I saw was that my clients didn't have enough clothes for the way they really lived. It was a quantity problem. Take my client, for example. She was a self described jeans and T shirt woman, but only had one pair of jeans and, you know, that whole a closet full of clothes but nothing to wear thing. I can't tell you how many times I heard it or saw it, but the issue was rarely that my clients truly had nothing. It's often that they had too many things for some parts of their lives and not enough for others. Specifically, they had too much for things they didn't do all that often and not enough for the things they did all the time, which made it very, very difficult to get dressed, but also frustrating because they could see the clothes, but they were still struggling. I often say that your wardrobe isn't all the clothes you own, it's all the things you can and do wear. So, yeah, you might have 20 pairs of dress pants for work, and that's a lot, but they don't help you if you're working from home and you just want to be comfortable. That's an example of too much of the wrong thing. On the other hand, I've worked with women who struggled to get dressed for Zoom meetings, especially when Covid happened and everybody went online. Right. Mostly they struggled because they didn't have tops that looked polished for work and appropriate for work, but weren't too dressy, because, let's face it, nobody believes you're wearing a blazer in the comfort of your own home. Right? And I remember asking one of these clients how often she had Zoom meetings just to get an idea of how big this problem was. And she told me that was basically her job. She had them all day, every day, and she was rotating through three tops and beginning to get the feeling that it was becoming noticeable to her clients. This is an example of not having enough of the right thing. That's the first part of spending your money where you spend your time making sure the distribution of your wardrobe roughly matches the distribution of your time. The other part, though, is about the quality of the right things. What I have seen a million times over the years is women willing to invest in really special pieces, but going as cheap as possible when it comes to their everyday wardrobes. Let's go back to that client for a moment. She was willing to spend 40 to 60% of pretty much her annual budget on something that would be worn a handful of times at most. But she only wanted to spend 10% or less on the piece that defined her style. If you describe yourself as a jeans and tee woman, shouldn't you be buying good jeans and more than one pair? I think so. I think this goes back to looking at our everyday lives and by extension, our everyday wardrobes as placeholders until the good stuff comes along. I remember working with a client who was feeling frumpy and kind of intimidated by the women in her neighborhood or which fair because we did not live in the most come as you are, no judgment here kind of place. It was tough, but she was struggling because she lived in athleisure clothes, leggings, sweatshirts, tees, and she didn't want to give those up. They were comfortable, they were practical for her life. But she didn't understand why she was wearing the same things as the women around her, but they looked put together while she didn't. She kind of thought that maybe she just didn't look good in athletic clothes. Maybe she needed a little bit more structure to dress up more. But when we went through her closet, that was not the problem at all. The problem was that all of her athleisure was low quality to begin with and then had been worn to death. Everything was faded, stretched out, pilly, like the whole thing just needed a refresh. When she and I went shopping, we were not limited by a tight budget, so we did a little shopping and then I took her to Athleta, knowing that we could find some nicer athleisure pieces there. She had total sticker shock and kept saying things like, I would never pay that much for leggings or I'm not walking the dog in a hundred dollar sweatshirt. The price tags were personal for her that day. I convinced her just to try a few things on, and they looked amazing on her. They had better shape and structure and style than what she had been wearing. And she admitted she would not feel out of place in these clothes. But then she kind of leaned into me and said, but we can find These things cheaper. Right. And at that point, I just had to ask, like, what? What's up? Because, again, while I was very respectful of budgets, we had already been to Nordstrom, where she'd spent over a thousand dollars on two pairs of jeans, few pairs of shoes, and a couple of tops. So it wasn't like she was opposed to investing in her clothes and that she couldn't do it. She just told me that she couldn't see spending that kind of money on clothes that didn't really go anywhere. Okay. Obviously, this was just a mental block. So I started asking questions like, well, how many days each week do you wear jeans? She said, well, maybe one or two. They're not that comfortable. Okay, how many days a week do you wear ballet flats? We just bought very expensive ballet flats. And she said, oh, not very often. I'm usually in my sneakers. I said, okay, well, where have you gone in the last week? What have you done? She said, oh, just kid stuff. Coffee, errands. Okay, what did you wear? I wore leggings and a sweatshirt. Finally, I was like, do you see that the majority of your life is spent in leggings and sweatshirts? And that you wear leggings and sweatshirts to the majority of places you go? So these clothes, they do go places. And she agreed with me. Then I said, so tell me how it makes sense to be in the worst clothes the majority of the time. And this is the part where I would love to tell you that she saw the light and we bought lovely athleisure things, and she lived stylishly ever after. But that is not what happened. Nope. What happened was she said, yeah, I can see that, but I just. I just can't. I can't do it. Okay. I tried my best. She just couldn't accept that these unexciting places and routine activities were. Were worthy of nice clothes. For her, they were just placeholders until her real life started. I want you to try something with me for just a minute. And I want you to imagine yourself in the middle of a circle, right? This big circle around you. That is the way you spend the majority of your days. Now, around you are some other, smaller circles. These are things you do, but not as often. Maybe they are going to concerts or traveling or fancy brunches, whatever. They're your circles. You do what you want. You can buy nice things for all of the smaller circles, but if you neglect the middle circle, the biggest one, you're missing the opportunity to look nice the majority of the time. When you put it that way, it doesn't make a whole lot of sense, does it? When we're afraid or unwilling to invest in better things for the way we really live, the quality of our wardrobes suffer. Quality means a couple of things here. Actual clothing quality, like the construction and longevity, as well as the visual quality or style. Clothing quality isn't always a given. I have a ton of issues with the quality of today's clothing, and one is that often you don't really get better quality if you spend a little bit more. You have to spend a lot more to really see the difference. So I can see why women don't want to invest that. But there are things that investing a little bit more will get you better quality and especially jeans and shoes. But when it comes to visual quality or style, a little more money almost always gets you a little bit more, or at least a little bit better style. I find graphics to be a good example of this. Like graphic tees or graphic sweatshirts most of the time. Not always, but most of the time. The cheaper the item, the cheesier the graphic. The more expensive the item, the more stylish the graphic. Again, I am not saying that all cheap graphics are terrible and all expensive graphics are great. Nope, not at all. But if you want an easy way to stay on the cool and quirky versus corny and cheesy side of graphics, invest a little bit more. Another way style is impacted, and this is what I see most often, is that everything can get super basic when you spend as little as possible. My Athleisure client had plain leggings, plain tees, plain hoodies, plain sweatshirts, plain, plain, plain. Nothing had any interest. Now, you know I love sweatshirts, and I have got basics from Old Navy and Gap, and there's nothing wrong with them. But my most stylish versions are not. Those are from Anthropologie and Nordstrom, Bowdoin, Evereve, Marine Layer. None of them were $20, and yet they're some of the best money I've ever spent. Because not only do I feel like me in them, I feel like the best version of me, an elevated version of me. And they're not things that I've been able to get inexpensively. Trust me, I have tried. Part of spending your money where you spend your time comes down to cost per wear. I don't hesitate to spend on sweatshirts because I know I'll wear them and get my money's worth, unlike fancy dresses that would only be worn a handful of times. But part of it is just wanting to feel as good as possible as often as possible. And if that means spending a little bit more, it's 100% worth the investment. So here's what I want you to do if you're ready to feel as good as possible as often as possible. First, you have to accept that the places you go most often and the things you do most frequently are in fact your real life. That's it. This is the only one you get. Those things are not simply filling time until something better comes along. Once you accept that, you can decide if you're ready to invest a little bit more in it or not. But if you keep buying clothes for fancy dinners out but you haven't been to a nice restaurant in years, you're going to keep filling your closet with the wrong stuff and you and not have cute outfits to go to. I don't know. Chick fil a in Second thing to do is figure out if your issue is in the quantity of clothes you have for your real life or in the quality. Here's an easy way to tell if you struggle to get dressed, it's probably a quantity problem. If you can get dressed just fine, but you're underwhelmed with the results, chances are it's a quality problem. Finally, solve the right problem. If it's quantity, ask yourself what would make it easier to get dressed? Is it more jeans? Are you missing layers? Do you need shoes? What are you missing? If it's quality, start by just looking at nicer versions of the things you already love to wear. So if it were me, and I love a good sweatshirt, instead of looking at Old Navy's options, I would look at Nordstrom or Anthropologie. If you find something that lights you up and it's in your budget, give yourself permission to splurge a little. If you're having a hard time justifying it, look on sites like Poshmark or ebay for similar items. Maybe you can't get the same thing, but you can probably find something along that vein. This can be a great way to test the waters of buying just a little bit better. It can be hard to change your thinking about spending on everyday clothes instead of special things, but I know that when you start to feel more stylish more often, it's an easy practice to keep up with. And over time, you'll find you're wearing more of what you own and spending less on clothes you never reach for. Oh, and in case you're wondering what happened to my client who wanted to blow 60% of her budget on a single dress for a single evening. I found her a fabulous gown on clearance for under a hundred dollars and and then I put her in the most expensive pair of jeans she'd ever worn. She emailed me a couple of weeks later to tell me that after our shopping trip, she bought two more pairs of that same jean. That, my friend, was money well spent. All right, that's it for this episode of Summer Shorts. I hope it inspires you to right size your wardrobe and invest in clothes for the way you really live. It's true, your everyday really does matter, so get dressed for it. Thanks for listening and I'll see you next week.
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Episode: Spend Smarter, Look Better
Host: Jennifer Mackey Mary
Date: August 21, 2025
In this impactful "Summer Shorts" episode, host Jennifer Mackey Mary dives into a practical wardrobe strategy: "Spend your money where you spend your time." Sharing personal anecdotes and professional insights, Jennifer explains how most women misallocate their wardrobe budgets, often overspending on special-occasion pieces and underinvesting in the clothes they actually wear daily. The episode offers tactical steps to right-size your wardrobe, improve daily satisfaction with your style, and spend smarter—without sacrificing confidence or comfort.
During Covid, clients had only 3 “work-appropriate” tops for constant Zoom meetings—another case of not having enough of what’s needed most.
Practical Tip:
Ensure your wardrobe categories match how and where you actually spend your days.
Higher-priced items aren’t always better quality, but in certain categories (jeans, shoes, statement sweatshirts), it pays off.
Investing in quality can mean finding more interesting, “you”-reflecting pieces, not just basics.
Quote:
"If you want an easy way to stay on the cool and quirky versus corny and cheesy side of graphics, invest a little bit more." (A, 15:11)
Jennifer closes by reminding us:
"Your everyday really does matter, so get dressed for it." (A, 19:37)
For listeners seeking a relatable, implementable approach to style, this episode delivers both strategic guidance and reassuring permission to honor your real life—every day, in every outfit.